5-氯硫代苯-2-甲酸乙酯 | 5751-82-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-氯硫代苯-2-甲酸乙酯
• 中文别名: 2-氯噻吩-5-甲酸乙酯；5-氯噻吩-2-甲酸乙酯
• 英文名称: ethyl 5-chlorothiophene-2-carboxylate
• CAS: 5751-82-6
• 化学式: C₇H₇ClO₂S
• mdl: MFCD00051732
• 分子量: 190.65
• InChiKey: BMOKMXXTOZFEIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  70-71°C 1mm
• 密度：
  1.312±0.06 g/cm3(Predicted)
• 闪点：
  70-71°C/1mm
• 稳定性/保质期：
  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319
• 储存条件：
  避光，存于阴凉干燥处并密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Ethyl 5-chlorothiophene-2-carboxylate
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P362: Take off contaminated clothing and wash before reuse
P321: Specific treatment (see on this label)
P332+P313: If skin irritation occurs: Get medical advice/attention
P337+P313: If eye irritation persists get medical advice/attention

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Section 3. Composition/information on ingredients.
Ethyl 5-chlorothiophene-2-carboxylate
Ingredient name:
CAS number: 5751-82-6

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H7ClO2S
Molecular weight: 190.6

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen chloride, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-氯硫代苯-2-甲酸乙酯 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 以68.6 %的产率得到5-氯-2-噻吩甲酰肼
  参考文献：
  名称：

  作为阿兹海默症兰尼碱受体和乙酰胆碱酯酶双重抑制剂的腙的设计、合成和评价

  摘要：

  阿尔茨海默病 (AD) 涉及神经元丢失、斑块和神经原纤维缠结形成以及神经元 Ca 2+稳态紊乱，这会导致严重的痴呆、记忆丧失以及最终可能导致死亡的思维和行为紊乱。钙失调和低乙酰胆碱水平是阿尔茨海默病进展的两个主要机制。单分子同时抑制钙振荡（储存过载诱导的 Ca 2+释放 [SOICR]）和乙酰胆碱酯酶 (AChE) 可能为 AD 治疗带来新的希望。在这里，我们将一些丹曲林衍生物描述为兰尼碱受体和 AChE 的双重抑制剂。两个系列的芳香族酰腙/磺酰腙衍生物 组被设计和合成。在这项研究中，使用丹曲林和多奈哌齐作为阳性对照，评估了目标化合物在体外抑制 SOICR 和 AChE 的能力。化合物22a对 SOICR（抑制率 (%) = 90.1，IC 50 = 0.162 μM）和 AChE（抑制率 (%) = 93.5%，IC 50 = 0.372 μM）表现出优异且平衡的抑制效力。对接模拟表明，

  DOI：

  10.1016/j.bioorg.2023.106432
• 作为产物：
  描述：

  2-噻吩甲酸 在 磺酰氯 、 硫酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 5-氯硫代苯-2-甲酸乙酯
  参考文献：
  名称：

  一种2-氯噻吩-5-甲酸的合成方法

  摘要：

  本发明公开了一种2‑氯噻吩‑5‑甲酸的合成方法：噻吩‑2‑甲酸与乙醇在浓硫酸作用下，经酯化反应生成噻吩‑2‑甲酸乙酯；噻吩‑2‑甲酸乙酯在二氯甲烷、N,N‑二甲基甲酰胺体系中，与磺酰氯进行氯化反应生成2‑氯噻吩‑5‑甲酸乙酯；2‑氯噻吩‑5‑甲酸乙酯在碱性物质作用下进行水解反应，生成2‑氯噻吩‑5‑甲酸；本发明以噻吩‑2‑甲酸为原料，经过酯化，氯化，水解，得到2‑氯噻吩‑5‑甲酸，本发明方法新型，操作简单，原辅料便宜易得，反应温和、选择性高，产品收率和纯度高，“三废”量少，更环保，适合放大生产；

  公开号：

  CN115557928A

文献信息

• Triazinone compound and T-type calcium channel inhibitor
  申请人：NISSAN CHEMICAL INDUSTRIES, LTD.

  公开号：US09403798B2

  公开（公告）日：2016-08-02

  There is provided a novel triazinone compound that has an excellent T-type voltage-dependent calcium channel inhibitory activity and is specifically useful for treatment of pain. A compound of Formula (I), a tautomer of the compound, a pharmaceutically acceptable salt thereof, or a solvate thereof: where each substituent is defined in detail in the description or claims, for example R1 is H or C1-6 alkoxy, etc., each of L1 and L2 is independently a single bond or NR2, etc., L3 is C1-6 alkylene, etc., A is C6-14 aryl or 5 to 10-membered heteroaryl which is optionally substituted, etc., B is C3-11 cycloalkylene, etc., D is C6-14 aryl or 5 to 10-membered heteroaryl which is optionally substituted, etc.

  提供了一种新型的三嗪酮化合物，该化合物具有优良的T型电压依赖性钙通道抑制活性，特别适用于治疗疼痛。公式(I)的化合物、该化合物的tautomer、药用可接受的盐或溶剂: 其中，每个取代基在说明或权利要求中有详细定义，例如，R1是H或C1-6烷氧基等，L1和L2各自独立为单键或NR2等，L3为C1-6亚烷基等，A为C6-14芳基或5至10元杂芳基，该芳基可被选配地取代等，B为C3-11环烷基等，D为C6-14芳基或5至10元杂芳基，该芳基可被选配地取代等。
• 4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors
  作者：Laurent Gavara、Alice Legru、Federica Verdirosa、Laurent Sevaille、Lionel Nauton、Giuseppina Corsica、Paola Sandra Mercuri、Filomena Sannio、Georges Feller、Rémi Coulon、Filomena De Luca、Giulia Cerboni、Silvia Tanfoni、Giulia Chelini、Moreno Galleni、Jean-Denis Docquier、Jean-François Hernandez

  DOI：10.1016/j.bioorg.2021.105024

  日期：2021.8

  (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs

  在革兰氏阴性菌中，对 β-内酰胺类抗生素产生耐药性的主要机制是产生一种或多种 β-内酰胺酶 (BLs)，包括令人担忧的碳青霉烯酶。尽管这些酶的抑制剂最近上市，但它们仅针对丝氨酸-碳青霉烯酶（例如 KPC 型），尚无临床上有用的抑制剂来中和金属-β-内酰胺酶 (MBL) 类。我们正在开发基于 1,2,4-三唑-3-硫酮支架的化合物，该支架以原始方式与 MBL 的二锌催化位点结合，我们之前报道了其产生广谱抑制剂的潜力。然而，到目前为止，在微生物测定中只能观察到适度的抗生素增强作用，需要进一步探索以改善外膜渗透。这里，我们合成并表征了一系列在杂环的 4 位具有不同官能化烷基链的化合物。我们发现在烷基链末端存在羧基会产生有效的 VIM 型酶抑制剂K i值在 μM 到亚 μM 范围内，并且该烷基链必须更长或等于丙基链。该结果证实了羧基官能团对 1,2,4-三唑-3-硫酮杂环的 4-取代基的重要性。如
• A Simple and Facile Carboxylation Method and Its Application for Synthesis of Liquid Crystals
  作者：Adam Shih-Yuan Lee、Chih-Chiang Wu、Li-Shin Lin、Hsiu-Fu Hsu

  DOI：10.1055/s-2004-815944

  日期：——

  Sonication of a mixture of magnesium powder, 1,2-dibromoethane, aryl bromide and diethyl dicarbonate in THF followed by treatment with BF3·OEt2 at room temperature afforded aryl ester with reasonable yield. A series of aryl bromides were investigated and transformed to their corresponding aryl esters under the reaction conditions.

  将镁粉、1,2-二溴乙烷、芳基溴和二乙基二碳酸酯的混合物在THF中进行声波处理，随后在室温下用BF3·OEt2处理，以合理产率得到了芳基酯。研究了一系列芳基溴，并在反应条件下将其转化为相应的芳基酯。
• Direct Conversion of Aromatic Ketones to Arenecarboxylic Esters via Carbon–Carbon Bond-Cleavage Reactions
  作者：Guodong Yin、Meng Gao、Zihua Wang、Yandong Wu、Anxin Wu

  DOI：10.1246/bcsj.81.369

  日期：2008.3.15

  Aromatic methyl ketones, β-keto esters, and trifluoromethyl-1,3-diketones can be directly converted to arenecarboxylic esters via carbon–carbon bond cleavage of pyridinium iodide intermediates in t...

  芳香族甲基酮、β-酮酯和三氟甲基-1,3-二酮可以通过碘化吡啶中间体的碳-碳键断裂直接转化为芳烃羧酸酯...
• Substituted oxoazaheterocyclyl compounds
  申请人：AVENTIS PHARMACEUTICALS INC.

  公开号：US20040102450A1

  公开（公告）日：2004-05-27

  This invention is directed to oxoazaheterocycyl compounds which inhibit Factor Xa, to oxoazaheterocycyl compounds which inhibit both Factor Xa and Factor IIa, to pharmaceutical compositions comprising these compounds, to intermediates useful for preparing these compounds, to a method of directly inhibiting Factor Xa and to a method of simultaneously directly inhibiting Factor Xa and Factor IIa..

  这项发明涉及抑制因子Xa的氧杂杂环化合物，抑制同时抑制因子Xa和因子IIa的氧杂杂环化合物，包含这些化合物的药物组合物，用于制备这些化合物的中间体，直接抑制因子Xa的方法，以及同时直接抑制因子Xa和因子IIa的方法。

表征谱图